1,508 results for sissy training

BBC Birthday Surprise

Taboo Phone Chat

I love sissies and when you are training them to be the best dressed cock sucking sissy they can possibly be, you grow really close!

All my sassy sissy sluts are my like my best friends so when my girl, Sam had her birthday, I threw her the hottest sissy bash you had ever seen!

And the main event was the big black cock strippers!

All the girls had a blast but Sam was the center of attention!

Her sexy sissy panties didn’t stay on long and for this event, we even let her take her cock cage off…because, let’s face it, when you have a giant black snake slithering in your sexy ass and another one looking so tasty as he is fucking your sissy throat…you can’t help but get dripping hard!

 

It feels so erotically slutty when you are getting dominated by dark meat from both ends!

 

Sissy Phone Sex

 

 

 

 

 

Sam loved backing into that dark thick cock and taking inch by inch deep in her sexy little sissy ass and having her stretched fuck hole filled with the steamiest load of thick milky cum! And all the other sissy sluts were fighting over who got to suck that chocolate syrup out of that tight fuck hole!

No one could blame her when her cock started to bulge as that big black dick made his way past her pretty mouth! And once again, the other sissy sluts jumped at the chance to suck every drop of Sam’s sticky cum.

It was definitely the best birthday for a sissy slut that is addicted to big clack cock!

Put Your Fucking Panties On

Sissy Girl Training

“How many times do I have to order you to put those frilly, lacy little panties on?” I slapped my new little sissy across the face. She needed a little convincing, it would seem. I had just stuffed her clitty into a chastity cage and she was absolutely being a disobedient little bitch.

Grabbing her up by her hair, which we would be shaving off and growing in anew, I forced her face down to my bare toes. I forced her to suck, lick, and worship my pretty toes and perfect soles. I knew all of this was turning her into a horny little whore, and she was going to have to learn the hard way that playing with me means complete obedience.

I forced my new little slut toy to her feet, and handed her the panties again. Again, she refused. I backhanded that little bitch, and bent her the fuck over immediately! One of my loyal sissy girls handed me my large, corkscrew butt plug. This would not be slipping from her shit hole at any point. She started to cry and beg, but I only laughed. In the end, I’d break this one too.

My Toilet Slave, A Taboo phone chat

taboo phone sex

A chance rendezvous with a toilet save would lead to some very taboo phone chats. In this era, I don’t have much time to meet guys. So I took to finding online men who were sissy sluts and might just pay up. I was about to give u hope at finding a pay pig, until he messaged me. 

“Can this lowly slave drink your piss mistress?” 

I was flabbergasted, he wanted to drink my piss? Oh, and it had to be right when I woke up piss. He was offering $500 and I was looking at a new Tory Burch handbag. I could sell my pee. We could make it contactless. But then My messages dinged once again. Would I be willing to meet and piss down his throat for two thousand dollars? I don’t know this man from Adam, so I made him Video call me and each call would cost him. 

I could buy that sexy Burberry tote I was looking at and some Burberry sneakers too! Turns out this was a real Toilet sissy boi who needed his hot Mistresses piss! 

The cash started flowing and I agreed to piss in Sissy La-las mouth last weekend. Let me tell you. I brought my best friend with me, she agreed that someone should tape him for blackmail, and well we are young so for safety purposes too. I was staggered by the Hotel room he got us and was astonished that the Toilet boy wouldn’t be here till the morning. Bestie and I enjoyed chilled champagne and room service until the early morning hours. I woke up to my phone buzzing and it was my personal potty ready for his/her? Piss deposit! It happened very quickly and the piss was hot and dark yellow as this slave gulped it down on camera! Wearing the cutest panties and sun dress too! I very much enjoyed giving some Sissy humiliation training.

Such a pretty girl!!!

sissy humiliation training

Today marked the beginning of your sissy humiliation training. You come to me on your knees eager to please your mistress. You are instructed to step into the shower and shave every bit of hair on your disgusting man body. When you come out you find some lotion and a pretty dress for you to put on. You walk into my room and kneel at my feet. I lube up a pretty pink butt plug and press it into place. I watch you squirm as you are getting used to the sensation of something that large in your ass. I apply your makeup and hand you a wig to put on. I tell you that we are going out for the afternoon and to grab your purse. You get such a cute, confused look on your face and ask about panties. I laugh and tell you that you haven’t earned the right to wear them yet and that you will need to figure out how to keep your plug in place and cock down. I hand you some heels to step into that match with your dress and purse and out we go. I take you window shopping at the outdoor mall knowing that each step is a special kind of torture for you. At the end of the day I hear a sigh of relief from you as I allow you to remove your plug for the last time. From this day on there will always be either a plug or a hard cock in that asshole.

 

She Is Becoming A BBC Cock Whore

mistress phone sex

Everybody loves BBC. But I have found that sissies seem to love it more than I do. The only problem is that sissies get overly excited and must be trained to control themselves. Nancy was no different and in order to get her under control she would need hands on training. I dressed her in some pretty pink nylon panties and matching lipstick. I told her I had a surprise in my room and she practically danced as she followed me. There was a beautiful man with a giant BBC. I instructed Nancy to watch as I played with that big black cock and to never move her eyes from mine. I sat Nancy down on the floor in my room and got down on my knees to admire that big black beauty. My god it is so wonderful. I could see Nancy trying to divert her eyes and quickly reminded her that her eyes were to remain on me. She watched me take that massive beast deep in my throat as he proceeded to fuck my throat hard. As soon as he came in my mouth, I held that giant load without swallowing. Nancy had been so good that I motioned her over and opened her mouth and dumped my mouthful of big black cum into hers. I made her hold it in her mouth until I told her she could swallow. She did so without hesitation, so I wanted to reward her. After fucking that beast, I let her clean that massive, beautiful, black cock with her tongue and then clean my cum filled cunt. My sweet Nancy is going to become a BBC whore.

BBC for me and you

BBC sissy trainer

Being a BBC sissy trainer has its advantages. You see I get to play first before I will allow you the pleasure of having a BBC service you. I love to suck their giant heads into my mouth and feel them stretching my throat as they use my head for a pocket pussy. Feel that giant slab of man meat force my cunt lips open as he takes me as a conquest. Then when my appetite has been quenched I will allow you to suck their cocks clean or allow you the pleasure of them filling your tight ass. You see Mommas’ needs will always be filled before your sissy ass even gets considered. I do enjoy watching you take a new cock in your mouth and try to swallow them. Hearing you choke and gag as you are getting used to his size. Watching your pretty face turning red and purple as he leaves his cock in your throat for a second longer. Watching you squirm as he is behind you lining his massive fuck tool up with your sweet ass. Hearing you screaming as that cock rocket breaches your small asshole and tears you up. Finally to hear the satisfied moans and groans as he is getting closer and closer to bathing your insides with his hot baby batter. Me not allowing you to clean up because I want to put a plug in your ass to ensure that none of that delicious cum leaks out. I love training new sissys to enjoy BBC as much as I do!

Just The Phone Dominatrix You Need

phone dominatrix

Hello, wannabe sluts! If you’re looking for a sissy phone dominatrix, look no further! I think you can probably tell by reading my blogs that I love training sissies and turning them into the best versions of their feminine selves. Do you need a little bit of help from someone who will be loving, yet firm? I won’t ever be mean and nasty to you, but I’ll tell you how it is and I won’t let you off the hook with broken promises, etc. By the time I’m done with you, you’ll be an even better sissy slut than you ever thought you could be.

The first thing you need to realize is that you are not in control once you call me to be your sissy trainer. You have to listen to me. You have to do what I tell you to do, no questions asked. You have to put your trust in me because I’m only going to tell you to do things that will be good for you and that you’ll enjoy. I won’t ever steer you in the wrong direction, my little sissy slut. I’m ready and willing to make your dreams come true, sissy!

Humiliation Phone Sex With a Sadistic Mistress

humiliation phone sex

Someone with a tiny lil clitty like you have isn’t good for much other than humiliation phone sex. And I hope that you know our humiliation call is going to be more than me just laughing at your poor excuse for a cock. It’s going to involve me getting you all dressed up so you can learn what it’s really like to be treated like you don’t have a dick. You’ll be treated like you are a woman completely when you’re on the phone with me. And if you’ve never gotten your pussy fucked, get ready because that’s totally something you’ll be doing. And speaking of getting ready for your pussy being fucked – do you have a dildo to play with? If not, you need to get on a website right now and order one. That way you can tell me it is on the way when you call me. It’ll make me so happy to know that I’ll be the woman to teach you all about being fucked. Once you’re used to that, I can pimp you out for bachelor parties and poker games dressed as a maid or cocktail waitress. Are you ready for your training? Let’s get this party started!

Forced Feminization With Queen Presley

Forced FeminizationI know it’s your first day as my sissy bitch, but don’t think that I’ll go easy on you. You came to me for some forced feminization, but you’ll be taking a lot more than that in your little ass. Let’s start by grooming you; every single part of you will be shaven, except for your hair and your eyebrows. Your hair will be grown out, or maybe we’ll shave it off too and put you in some of my beautiful wigs. You’re going to have bald little balls as I turn that tiny prick into a sweet little clit.
On goes your small clit cage. That’s right, sweetheart. Queen Presley decides if and when you cum, and today is not that day. Now, lets put you in these panties; silken and pink, just like your princess heart. Your bralette will match, silky pink, pretty. We’ll have to fill your bra until your tits come in; that’s right, I’m putting you on hormone replacement therapy.
You don’t want to really be a girl? Too bad, filth. You came into my castle, not shut up while I give you your first estrogen dose. Good. Up go your matching silk pink stockings, with a lace garter to match. Which gown shall I put you in? How about this pastel yellow baby? It goes with your beautiful eyes.
Now come here, let’s put this black wig on you, to pale you out. I’ll braid pink flowers into it. Oh, and bend over. Let me slide those silken panties aside to put in this pretty butt plug! It’s got a perfect pink diamond on the plug, so when you bend over for bare bottom spankings, I can show you off.
That’s my beautiful girl. Into these black heels you go. They lace up your calves. You’re lovely enough. Come and sit by me in court; we’ll giggle behind our fans as we peruse and pick out pricks for me to play with later. Come on, Princess. What a good girl.

Sissy Slave Training

He Made Me Submit

 

mistress phone sex

Oh my, you will need to sit down for this story. You know I am a Mistress that takes men and owns them. Making them my slaves to do with what I please. Make them service all of my needs. I am ruthless and proud as I put them in sissy panties and have them lick my juicy wet pussy until I orgasm all over their faces. Of course, I must also train them on the ways of pleasing a cock. I teach them to suck and fuck until they are my little masters. Now listen I had one of my favorites over for some training. He is awesome and has a gigantic cock between his legs, so I was super excited about this one. I started by having him undress me and lay me on the bed. He started licking my cunt and it was the most fabulous thing I have ever felt with a tongue. I immediately wanted more and moved his hips up to my mouth so I could suck on his cock while he continued to eat Mistress Francis’ pussy. His cock was so big and thick, and the mushroom head even had me stretching my mouth to take it all in. As I was enjoying his dick and his tongue, he casually moved me onto all fours and stuck his thick cock deep inside my ass. He filled it completely and I could feel my ass stretching, but it felt so good I couldn’t even discipline him. I mean he had done this without even asking. But I did nothing. Not even when he pushed my face to the bed and continued pumping my ass. I just let him have full control. That big thick cock on that handsome man took this Mistress and made her his little puppet as I submitted to his every desire.